Find short term rentals in Chesapeake, VA at the best prices
561 available short term rental offers
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Best Short term and Weekly rentals in Chesapeake, VA
Chesapeake, VA
29/06 – 03/08
$204/nighttotal: $7140 (35 )
The Norfolk Nomad: Spacious 4br Near Downtown, Odu
1 2
apartment , Norfolk
This four-bedroom, two-bathroom flat in Norfolk is located in a family-oriented district, offering generous space and proximity to local attractions, with easy access to parks and recreational areas suitable for children. This residence accommodates up to eight guests and features essential amenities such as air conditioning, internet, a kitchen, and parking, making it a comfortable base for exploring Norfolk's offerings.
9.7 251 reviews
Chesapeake, VA
27/06 – 04/07
$342/nighttotal: $2394 (7 )
Zen Quiet Massage Therapist Home/near Downtownevms
1 2
apartment , Norfolk
This Norfolk bed and breakfast is conveniently located just a mile or so from the city centre, with easy access to the Virginia Beach Town Centre and Oceanfront Boardwalk. The property has received excellent ratings for cleanliness, location, and overall guest experience. The accommodation offers a private room with a Zen-like atmosphere, perfect for relaxation. It can comfortably sleep up to four guests and features a full kitchen, a large bathroom with a rainfall shower, and access to a shared garden with a grill and beach chairs. Guests can enjoy additional amenities such as on-site massage therapy, kayak rentals, and a large jacuzzi tub.
Chesapeake, VA
29/06 – 03/08
$197/nighttotal: $6895 (35 )
Fairfax Manor Pearl Suite
1 2
apartment , Norfolk
This one-bedroom flat is located in the Ghent district of Norfolk, a short walk from CHKD and EVMS, and offers convenient access to downtown Norfolk's attractions. This accommodation allows pets, features a private backyard, a fully equipped kitchen with a fridge and microwave, air conditioning, high-speed WiFi, and a private entrance with keyless entry, accommodating up to two guests.
9.9 137 reviews
Chesapeake, VA
25/09 – 30/09
$327/nighttotal: $1635 (5 )
Beautiful 3bdrm Near Beach, Wi-fi & Parking
3 4
apartment , Virginia Beach
This three-bedroom home is situated just 7.5 kilometres from Virginia Beach Oceanfront and 2 kilometres from Town Center, offering a convenient location for exploring the area. The property consistently receives excellent ratings for its cleanliness, location, and overall guest experience. The apartment comfortably accommodates up to six guests and is fully furnished with modern amenities like a dishwasher, air conditioning, and a 55-inch flat-screen TV. Guests can enjoy a range of entertainment options, including foosball, board games, Netflix, and Hulu, as well as unique experiences like private paint parties, crabbing excursions, and paddle board rentals.
8.8 40 reviews
Chesapeake, VA
24/07 – 26/07
$405/nighttotal: $810 (2 )
Cozy Get Away Home
1 4
apartment , Norfolk
This Norfolk holiday home enjoys a central location, within 3.2km of the Waterside District and Norfolk Zoo, and a short drive from Norfolk Premium Outlets and the oceanfront. Sleeping four guests, this three-bedroom, two-bathroom property boasts air conditioning, parking, a kitchen equipped with a fridge, freezer and microwave, plus excellent cleanliness ratings and Wi-Fi access.
9.2 13 reviews
Chesapeake, VA
19/07 – 18/10
$164/nighttotal: $14924 (91 )
The Hive
1 1
apartment , Norfolk
This three-bedroom, two-bathroom flat in Norfolk's Berkley district is situated just 160 metres from Sentara Hospital and the Norfolk Naval Shipyard, with the Elizabeth River also nearby. This well-appointed apartment accommodates up to six guests and features modern décor, a fully equipped kitchen with high-quality cookware, comfortable sleeping arrangements, high-speed Wi-Fi, smart TVs, and a basement game room with a pool table.
9.0 2 reviews
Chesapeake, VA
01/07 – 31/07
$230/nighttotal: $6900 (30 )
Sojourn At Colley Manor Unit 2 Sleeps 4
2 2
apartment , Norfolk
Colley Manor Unit 2, a two-bedroom apartment in Norfolk, is conveniently located 10.6 km from the Norfolk Botanical Garden and 14.3 km from Topgolf Virginia Beach. This 93 square metre self-catering property sleeps six guests comfortably and offers free Wi-Fi, a fully equipped kitchen with dishwasher, laundry facilities, cable TV, air conditioning, and parking.
9.6 110 reviews
Chesapeake, VA
08/07 – 13/07
$324/nighttotal: $1620 (5 )
Walk To The Casino! Sleeps 8, Close To Everything
1 5
apartment , Portsmouth
This Portsmouth apartment is conveniently located within walking distance of the casino and a short drive (under 10km) to Norfolk, Virginia Beach, and Chesapeake. The property has received excellent ratings for its cleanliness, location, and overall experience, making it a great choice for travellers. The apartment has three bedrooms and two bathrooms, comfortably accommodating up to six guests. It comes with a fully equipped kitchen, laundry facilities, a private backyard, and smart home features, ensuring a comfortable and enjoyable stay.
9.9 59 reviews
Chesapeake, VA
31/07 – 31/08
$326/nighttotal: $10106 (31 )
2br Self Check-in, Fast Wi-fi
1 2
apartment , Chesapeake
This apartment is conveniently located just a short drive from Virginia Beach, offering easy access to the beach, boardwalk, and various attractions. It has excellent user, location, and cleanliness ratings, making it a great choice for travellers. The apartment comfortably sleeps four guests and features a spacious living area, two bedrooms, and a modern bathroom. It has a well-equipped kitchen with a fridge, freezer, microwave, dishwasher, and a washing machine and dryer, making it perfect for self-catering.
8.1 9 reviews
Chesapeake, VA
23/06 – 25/06
$254/nighttotal: $508 (2 )
Va Beach Zen Retreat House
1 3
B&B , Virginia Beach
The VA Beach Zen retreat house is located in Virginia Beach, just a short drive from Topgolf Virginia Beach and Mount Trashmore Park, making it a convenient base for exploring the area. The property has received very good user ratings and excellent ratings for location and cleanliness. The retreat offers a comfortable and relaxing stay with a 149 square metre floor area. Guests can enjoy a shared lounge area, a garden, and a terrace, as well as a fully equipped kitchen with a dishwasher, air conditioning, free Wi-Fi, and private parking.
9.8 24 reviews
Chesapeake, VA
08/07 – 13/07
$544/nighttotal: $2720 (5 )
3br, 6 Beds – Prime Stay Near Rivers Casino
1 5
apartment , Portsmouth
This fully refurbished three-bedroom house in Portsmouth is situated less than 3.2 kilometres from the Rivers Casino, offering easy access to Norfolk and Virginia Beach. Sleeping up to six guests, the property boasts a fully equipped kitchen with dishwasher, a modern bathroom, air conditioning, parking, and excellent Wi-Fi; deals are available for extended stays.
Chesapeake, VA
25/09 – 30/09
$449/nighttotal: $2245 (5 )
Free Breakfast. Indoor Pool & Hot Tub. Near The Virginia Beach Business District!
1 4
apartment , Chesapeake
This Chesapeake condo is situated a 9-minute walk from the Chesapeake Conference Centre and a 3-minute drive (approximately 1.6 km) from Greenbrier Mall, offering easy beach access. The one-bedroom, one-bathroom apartment sleeps four guests and includes a fully equipped kitchen, in-unit laundry, a swimming pool, jacuzzi, and free Wi-Fi; nearby attractions include the Veterans United Home Loans Amphitheatre and Waterside District.
Best Chesapeake, VA luxury short term rentals
9.6 87 reviews
Chesapeake, VA
25/09 – 30/09
$240/nighttotal: $1200 (5 )
Southern Charm
Warm And Welcome
2 4
apartment , Chesapeake
This Chesapeake apartment is located close to shopping and dining options, just a short distance from the interstate. It has received excellent ratings for its cleanliness, location, and overall user experience. The apartment can comfortably accommodate up to four guests and features a fully equipped kitchen, a private garden with a fire pit and gas grill, and a washer and dryer for convenience. It also includes child-friendly amenities such as a highchair, pack and play, and a dedicated kiddie corner closet.
Best Chesapeake, VA Short term rentals with a jacuzzi
Among the 561 accommodations in Chesapeake, VA, here are the 4 best rentals with a jacuzzi
Chesapeake, VA
16/08 – 27/08
$292/nighttotal: $3212 (11 )
Condo ∙ 1 Bedroom ∙ 6 Guests
1 4
apartment , Chesapeake
This apartment is conveniently located near the Virginia Beach business district and General Dynamics in Chesapeake, a 40-kilometre drive from the Virginia Beach oceanfront. The surrounding area offers easy access to both business and leisure activities, making it a popular choice for travellers. This one-bedroom apartment can accommodate up to six guests comfortably, with two queen beds and a sofa bed. Guests can enjoy a range of amenities, including a fully equipped kitchen, a swimming pool, a hot tub, a fitness centre, and free parking.
Chesapeake, VA
12/10 – 18/02
$140/nighttotal: $18060 (129 )
Serene Lodging With Indoor Fireplace
2 2
apartment , Virginia Beach
This Northwest Virginia Beach holiday home is situated 1.8km from Virginia Wesleyan University, within 5km of Sentara Leigh Hospital and Norfolk Premium Outlets. This 71-square-metre property offers two bedrooms, one bathroom, sleeps two guests, and includes a fully equipped kitchen, Jacuzzi, free Wi-Fi, and in-unit laundry facilities.
9.6 4 reviews
Chesapeake, VA
09/07 – 14/07
$663/nighttotal: $3315 (5 )
The Chesapeake Gray\n\nhistorical Waterside District\n20 Mins To Oceanfront \N\n
3 5
apartment , Norfolk
This Norfolk apartment is located within easy reach of both Waterside Festival Marketplace and Virginia Beach Town Center, offering a convenient base for exploring the city and its surroundings. The apartment is just a short drive from the beach, providing a perfect blend of urban convenience and coastal charm. The property is a spacious three-bedroom home that comfortably sleeps six guests. It offers a modern kitchen, a private backyard with a patio, and a jacuzzi, ideal for relaxing after a day of exploring the local attractions.
Chesapeake, VA
31/07 – 31/08
$115/nighttotal: $3565 (31 )
Serene Retreat - Hot Tub, Private Dock & Fire Pit
1 2
apartment , Portsmouth
This private, fully furnished flat, with its own entrance, is located in a peaceful residential area of Portsmouth, offering waterfront views and direct access to a private dock. This accommodation comfortably sleeps two, features a separate bedroom, a living room with a convertible sofa, a breakfast bar, air conditioning, a hot tub, and parking, making it ideal for a relaxing stay.
Frequently Asked Questions about short term rentals in Chesapeake, VA
What are the best short term rentals in Chesapeake, VA?
Best family friendly Chesapeake, VA Short term rentals
Among the 561 accommodations in Chesapeake, VA, here are the 4 best family friendly rentals
9.6 10 reviews
Chesapeake, VA
19/07 – 18/10
$71/nighttotal: $6461 (91 )
First Floor Guestroom
1 1
apartment , Chesapeake
This Chesapeake guesthouse offers a private, keyed-entry ground-floor room with a twin XL bed, ideal for solo travellers, and features a dedicated workspace with hardwired internet and Wi-Fi. The single-occupancy room includes a mini-fridge, 32-inch smart TV with Netflix, and ample storage, boasting excellent cleanliness and guest ratings, plus on-site parking, a swimming pool and garden.
9.4 313 reviews
Chesapeake, VA
23/06 – 25/06
$237/nighttotal: $474 (2 )
Olde Towne 4 Bedroom -2200 Sq Ft
1 3
apartment , Portsmouth
This Portsmouth apartment is located just a few hundred metres from the Strawbery Banke Museum and a 1 kilometre walk from Market Square, offering easy access to the city's historic district and attractions. The apartment has received excellent user ratings for its location, cleanliness, and overall experience. This two-unit property provides ample space for larger groups or families, with each unit containing two bedrooms and a bathroom. Guests can enjoy a range of amenities, including fully equipped kitchens, in-unit laundry facilities, smart locks, WiFi, TVs, and comfortable bedding.
Chesapeake, VA
12/10 – 18/02
$256/nighttotal: $33024 (129 )
Cheerful 2 Bedroom Home Near Virginia Wesleyan
2 2
apartment , Virginia Beach
This private two-bedroom townhome is located on a corner cul-de-sac lot in the Northwest district of Virginia Beach, offering a quiet setting just a short drive to First Landing State Park and the Virginia Aquarium. This 89 square meter residence accommodates up to four guests, featuring a fully equipped kitchen with a wine cooler, a screened-in porch, an extra-large sectional sofa, and high-speed WiFi, with contactless entry for a seamless self-check-in experience.
9.2 7 reviews
Chesapeake, VA
24/07 – 26/07
$680/nighttotal: $1360 (2 )
Walkable To The Casino And Family Friendly! 3 Bd/2 Ba, Full House, Sleeps 8
4 4
apartment , Portsmouth
This holiday home is located in Portsmouth, just 1.5 km from Rivers Casino Portsmouth, and within 10 km of Portsmouth City Park and Frank D Lawrence Stadium. It has consistently received excellent user ratings, making it a popular choice for travellers. The property offers 93 square metres of space and can comfortably accommodate up to 6 guests in its 3 bedrooms. The kitchen comes equipped with a fridge, microwave, oven, and dishwasher, while the garden provides a relaxing outdoor space. Guests can also enjoy free Wi-Fi, air conditioning, a terrace, and parking.
Best Chesapeake, VA lodging with parking
10 2 reviews
Chesapeake, VA
12/10 – 18/02
$203/nighttotal: $26187 (129 )
Sojourn At Colley Manor Unit 2
2 2
apartment , Norfolk
This Ghent flat in Norfolk is centrally located near Colley Avenue's restaurants and shops, within easy reach (by foot, bike, bus, or Tide light rail) of Norfolk city centre and major hospitals such as CHKD and Norfolk General Hospital, and a short drive (approximately 20-30 km) from Virginia Beach and Ocean View Beach. This 93-square-metre (1000 sq ft) two-bedroom, one-bathroom apartment sleeps four, offering self-check-in, a fully equipped kitchen (including fridge, microwave, and dishwasher), air conditioning, parking, and internet access; pack 'n' play and high chair rentals are available for families.
Chesapeake, VA
12/10 – 18/02
$131/nighttotal: $16899 (129 )
Steps To Elizabeth River & Dtwn! Portsmouth Condo
1 2
apartment , Portsmouth
This one-bedroom flat in Portsmouth is situated 8 minutes' walk from the Portsmouth Naval Shipyard Museum and 6 minutes' walk from the Commodore Theatre. This 56 square metre apartment accommodates two guests and features a fully equipped kitchen, air conditioning, on-site parking, and internet access, with a coin-operated laundry facility conveniently located nearby.
9.6 4 reviews
Chesapeake, VA
14/08 – 16/08
$319/nighttotal: $638 (2 )
Charming 1-bedroom In-law Suite With Functional Kitchen In Pleasant Portsmouth
1 2
apartment , Portsmouth
This one-bedroom flat in Portsmouth is situated a 19-minute drive from Town Point Park and 40 minutes from Chesapeake Bay, offering convenient access to the Chrysler Museum of Art and the Children's Museum of Virginia. This pet-friendly apartment accommodates up to three guests and includes on-site parking, complimentary Wi-Fi, air conditioning, and essential amenities such as towels, linens, and soap, with a check-out time of 12:00.
10 5 reviews
Chesapeake, VA
25/09 – 30/09
$396/nighttotal: $1980 (5 )
Historic Private Guest Apartment
2 4
apartment , Norfolk
This private apartment, located in Norfolk's West Freemason district, offers easy walking access to the riverfront, local shops, and dining establishments, with the Children's Museum of Virginia and Lamberts Point Golf Course approximately 3 kilometres away. This family-friendly flat accommodates up to four guests and features two bedrooms, one bathroom, air conditioning, a fully equipped kitchen with a fridge, microwave, and dishwasher, a separate living area, and an in-unit washer and dryer.